Cycloaddition Reaction of 1,4-Dihydronaphthalene 1,4-Epoxide with Cyclooctatetraene: Cope Rearrangement in an Adduct

Date

2008-01-01

Author

MENZEK, Abdullah
Kelebekli, Latif
ALTUNDAŞ, Aliye
ŞAHİN, Ertan
Polat, Fatos

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The reaction of 1,4-dihydro-1,4-epoxynaphthalene with cyclooctatetraene at 130 +/- 5 degrees for 14 days gave the four products 2a,3,3a,4,9,9a,10,10a-octahydro-4,9-epoxy-3,10-ethenocyclobuta[b]anthracene (13). 25-oxanonacyclo[10,10,2,2(5,9),1(14,21),0(2,11),0(3,10),0(4,6),0(13,22),0(15,20)] heptacosa-7,15,17,19,23,26-hexaene (14), 5,5a,6,6a,6b,6c,12a,12b,12c,13,13a,14-dodecahydro-5,14-epoxy-6,13-ethenocycloocta[3',4']cyclobuta[1',2',3,4]-cyclobuta[1,2-b]anthracene (15) and bis-adduct 16. The structures of the products were determined by spectroscopic methods. It was observed that adduct 14 undeergoes a Cope rerrangement. The Cope rearrangement of this adduct was investigated in the temperature range of -85 degrees to 100 degrees by NMR spectroscopy.

Subject Keywords

Stereospecific synthesis, Molecular design, High-pressure, c-13 nmr, Heterocycles, Derivatives

URI

https://hdl.handle.net/11511/67982

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.200890257

Collections

Department of Chemistry, Article

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Citation Formats

A. MENZEK, L. Kelebekli, A. ALTUNDAŞ, E. ŞAHİN, and F. Polat, “Cycloaddition Reaction of 1,4-Dihydronaphthalene 1,4-Epoxide with Cyclooctatetraene: Cope Rearrangement in an Adduct,” HELVETICA CHIMICA ACTA, pp. 2367–2378, 2008, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/67982.